Triphenylphosphine → 5-Iodo-2-(2-methoxyethoxymethoxy)benzyl bromide

HRID 2758Notes

Reaction equation

HRID 2758 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([CH:9]=1)[CH2:7]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]NC(=O)CCC(N)=O>C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])=[C:6]([CH:9]=1)[CH2:7][Br:36]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 9834204N-BromosuccinamideHCID 537134685-Iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol

Product 1

HCID 105971565-Iodo-2-(2-methoxyethoxymethoxy)benzyl bromide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol (7.5 g, 22 mmol) in 60 mL of THF at 15° C. is added triphenylphospine (6.35 g, 24 mmol) followed by N-bromosuccinamide (4.3 g, 24 mmol). The solution is stirred for 5 min. The solution is allowed to warm to ambient temperature. After 20 min, the solution is concentrated. The crude product is purified by column chromatography eluting with EtOAc:CH2Cl2 :hexane (3:1:6).

Workup

  1. waitAfter 20 min
  2. concentrationthe solution is concentrated
  3. customThe crude product is purified by column chromatography
  4. washeluting with EtOAc:CH2Cl2 :hexane (3:1:6)

Sources & evidence

ORD record
ord-fcd44485706940d6937ed2c6fbc98557
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Reaction notes

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